Diisopropylethylamine → N-{2-[4-(2-Cyclopentyloxy-pyrimidin-5-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

HRID 76204Notes

Reaction equation

HRID 76204 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH:2].Br[C:17]1[CH:18]=[N:19][C:20]([O:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:21][CH:22]=1.CCN(C(C)C)C(C)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:24]1([O:23][C:20]2[N:19]=[CH:18][C:17]([C:2]#[C:1][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=3)=[CH:22][N:21]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 49758716HCID 49758716, compoundHCID 86669621N-(1-(4-ethynylphenyl)propan-2-yl)acetamide

Product 1

HCID 56925027N-{2-[4-(2-Cyclopentyloxy-pyrimidin-5-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 33.1 mg (0.17 mmol) N-[2-(4-ethynyl-phenyl)-1-methyl-ethyl]-acetamide (I58.3) and 40.0 mg (0.17 mmol) 5-bromo-2-cyclopentyloxypyrimidine (I14.1) in 2.0 mL THF are added 11.6 mg (0.02 mmol) bis(triphenylphosphin)palladiumdichlorid, 1.57 mg (8.00 μmol) CuI and 56.0 μL (0.33 mmol) DIPEA. The reaction mixture is stirred at r.t. over night. The solvent is removed in vacuo and the residue is purified by HPLC (MeOH/H2O/TFA).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-082f8a11a6c54529a16876e06bae65c3
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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